(20S)-3,17β-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene | 102651-48-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (20S)-3,17β-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene
• 英文别名: (8R,9S,13S,14S,17S)-13-methyl-17-[(2S)-oxiran-2-yl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 102651-48-9
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: DVZRZZJKBCUJGQ-XVMXLUHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20S)-3,17β-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 以40%的产率得到(20R)-3,21-dihydroxy-17β,20-epoxy-19-norpregna-1,3,5(10)-triene
  参考文献：
  名称：

  3,17.beta.-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-trienes. Synthesis, rearrangement, cytotoxicity, and estrogen-receptor binding

  摘要：

  Diastereoisomers of 3,17 beta-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene have been prepared as potential antitumor agents. Both isomers undergo the base-catalyzed Payne rearrangement. The isomers were cytotoxic to mammalian cells in culture and were able to displace [3H]estradiol from binding sites in rat uterine cytosols with 1/7 and 1/70 the potency of estradiol. The reasons for this difference are discussed.

  DOI：

  10.1021/jm00158a039
• 作为产物：
  描述：

  17α-vinylestradiol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以39%的产率得到(8R,9S,13S,14S,17S)-13-甲基-17-[(2R)-环氧乙烷-2-基]-7,8,9,11,12,14,15,16-八氢-6H-环戊二烯并[a]菲-3,17-二醇
  参考文献：
  名称：

  3,17.beta.-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-trienes. Synthesis, rearrangement, cytotoxicity, and estrogen-receptor binding

  摘要：

  Diastereoisomers of 3,17 beta-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene have been prepared as potential antitumor agents. Both isomers undergo the base-catalyzed Payne rearrangement. The isomers were cytotoxic to mammalian cells in culture and were able to displace [3H]estradiol from binding sites in rat uterine cytosols with 1/7 and 1/70 the potency of estradiol. The reasons for this difference are discussed.

  DOI：

  10.1021/jm00158a039

文献信息

• 3,17.beta.-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-trienes. Synthesis, rearrangement, cytotoxicity, and estrogen-receptor binding
  作者：Julie C. Gill、Peter M. Lockey、Brian A. Marples、John R. Traynor

  DOI：10.1021/jm00158a039

  日期：1986.8

  Diastereoisomers of 3,17 beta-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene have been prepared as potential antitumor agents. Both isomers undergo the base-catalyzed Payne rearrangement. The isomers were cytotoxic to mammalian cells in culture and were able to displace [3H]estradiol from binding sites in rat uterine cytosols with 1/7 and 1/70 the potency of estradiol. The reasons for this difference are discussed.